


Truth or Dare

by kwrites



Category: Arrow (TV 2012)
Genre: F/M, M/M, Multi, NSFW, PWP, Prom, Smoaking billionaires, Smut
Language: English
Status: Completed
Published: 2015-05-02
Updated: 2015-05-02
Packaged: 2018-03-26 18:19:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,643
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3859906
Author URL: https://archiveofourown.org/users/kwrites/pseuds/kwrites
Summary: <blockquote class="userstuff">
              <p>A mishap on the way to prom leads to a different type of celebration for Oliver, Tommy and Felicity.</p>
            </blockquote>





	Truth or Dare

**Author's Note:**

> Started with a drabble prompt on Tumblr for "Smoaking Billionaires + Prom". Transformed into something a little different and a lot dirtier. ;) 
> 
> Dedicated to my trashy muse, Feli. I hope you enjoy.

Two minutes ago, Felicity Smoak had been full of nerves. But the good kind of nerves. The I’m-so-excited-for-prom-I-could-puke nerves. Not the ones that had taken over her body after stepping one foot into the extended limo Oliver had rented for prom.

 

No. Now she was full of panicky, heart-falling-into-your-stomach nerves.

 

Why? Because she had ripped her prom dress.

 

Only Felicity Smoak could rip her prom dress (her very expensive prom dress she might add) before leaving the premises of her home. _Ugh, for being the genius she was, she really had some less than finer moments._

 

Oliver and Tommy, of course, had thought the whole thing was hilarious.

 

Pre-dress fiasco, she had opened the limo door to a find them ready to greet her in a familiar position. They were each slouched in a corner of the car, jackets thrown aside carelessly, and large bottles of expensive champagne in hand.

 

She could tell Oliver had been fiddling with his collar, it was pulled lazily to one side, and more than of a few of the buttons had been undone. His eyes were shiny and wide, a tint of amusement within the vibrant green. He looked sinful.

 

They had both lit up at her arrival, Tommy throwing her an enthusiastic (and slightly slurred) “Felicity!”. Oliver’s appreciation at her arrival had been a bit more… demure. Though his eyes were just as bright as Tommy’s, they held a darker, more intent focus as they took in her smokey make-up and floor length dress.

 

Trying to distract herself from the heat of his gaze, she sighed - exasperated.  “You’re both already drunk?”

 

Tommy mock gasped, pointing a finger to himself. “Who me? I am an upstanding citizen Miss. Smoak and I do not appreciate the accusation.”

 

Felicity rolled her eyes and took one step into the limo.

 

That was it. That was all it took for her Donna Smoak-approved, midnight blue dress to get caught in the door and rip. From side to side. _Horizontally._ How did one even?

 

“Oh frack!”

 

And that’s where she was in the current time. Paralyzed, dress still stuck in the door, mouth wide open.

 

Oliver and Tommy’s eyes had both gone wide for a beat, before they both collapsed into themselves, heaving with laughter.

 

“Guys!” Felicity whined, “Stop laughing! What am I going to do! I can’t go to prom in front of the whole school like this and I obviously can’t sew it, I mean I don’t know if you have ever seen me sew anything but let me just tell you-”

 

“Felicity, breathe.” Oliver interrupted her. “It’s okay. It’s just a stupid dance. Honestly I’d be fine with just skipping it all together.” Tommy nodded his approval. He had been against going the entire time - they didn’t need a high school dance to have a good time. They had been getting into clubs for years. Those were real dance parties. They had only decided to go at Felicity’s insistence.

 

“But it’s prom! Aren’t we supposed to go have normal high school experiences and everything?” But Felicity’s voice was soft, already considerably calmer at a solution to her dress disaster.

 

Oliver shrugged, lifting his bottle of champagne towards her in salute. “Tommy’s dad is out of town. His house is open. We have endless amounts of free booze. Why don’t we go have our own prom at Tommy’s? The company is already infinitely better.” Felicity’s breath caught in the back of her throat at the smile that stole across his face. It was Oliver’s patented smirk. Mischievous and full of _promise_.

 

She caved. Of course.

 

\----------

 

As soon as she had stepped through the front door of the Merlyn mansion, Felicity had scurried to change. Anything to get her away from Oliver and Tommy’s wandering eyes. She had felt the heat of their gazes the entire limo ride back. After she had detached herself from the limo door, she had been left half naked, the dress barely covering her.

 

Felicity had quickly grabbed one of the bottles of Champagne from Tommy’s grip, taking a healthy chug that she continued to hold on to for the ride. But with the boys’ head start, they had become more and more relaxed and their discretion was… inexistent. They didn’t try to hide their obvious perusal of Felicity’s legs because, honestly, _damn_.

 

She couldn’t lie. She secretly loved it.

 

After she had pulled herself into a pair of stray clothes Tommy had lying around (from god only knows where or who, really) she sauntered out of the bathroom to find Oliver sprawled across the large sectional in the living room. He had ditched the dress shirt for his simple white tee, and fuck if that wasn’t one of Felicity’s favorite looks.

 

Tommy was, unsurprisingly, behind the bar mixing together what she could only assume would be hell in a glass. Finishing, he handed one off to Felicity, bringing Oliver’s and his own over to the sectional.

 

Tommy cleared his throat, raising his glass in their direction. “So, should we cheers to the end of high school or my father’s credit card for purchasing the limo that ripped Felicity’s dress and allowed us to skip the nightmare that is a high school prom?”

 

Felicity rolled her eyes, replying “I’m sorry that not all of us were born with silver spoons in our mouths and fake ID’s by the time they were 15. I spent all year studying for MIT, I wanted to do the whole high school experience right.”

 

Oliver waved off her comment. “Yeah, yeah, but now we’re here. So what are we going to do? Skinny dip? Naked twister?” He grinned. Oh, the possibilities.

 

“I like where your head’s at, buddy.” Tommy grinned.

 

Felicity sighed, exasperated. “We are definitely not playing naked twister.” Both boy’s faces immediately dropped. C’mon, did they really expect her to say yes?

 

But the more she thought about it, the more she realized that this was it. The end of high school. In a few short months she would be leaving to attend MIT in Boston, and although Oliver would be joining her to attend Harvard, Tommy would remain in Starling and their close little group that she had come to love so much would be ripped apart. Wasn’t this the time for wild, youthful experiences?

 

Feeling slightly emboldened, she smiled. “So, naked twister is definitely off the table… but what about truth or dare?” That was safer than naked twister - right? She groaned, either way - she was definitely going to need more alcohol.

 

Tommy looked like he had been about to protest, but had stopped himself short, eyes swinging to Oliver, finding him already looking over towards him. Felicity, slightly in awe, watched as they had an entire conversation without speaking a word.

 

After a beat, both boys smiled and turned back towards her. Oliver was the first to speak. “Great idea ‘licity. But I’m thinking shots first. In order to really make this interesting.”

 

Felicity didn’t really think that either boy needed more to drink, but her nerves were flaring after their silent conversation and she was more than ready to loosen up a bit more.

 

_God, she hoped Oliver was reaching for the Tequila. She really loved Tequila._ Looking up, she was greeted with a smug grin from Tommy and a look of faint surprise from Oliver. “I said that out loud, didn’t I?”

 

Oliver grinned, shaking his head.

 

This was going even better than he could have planned. And he had plans. Had since the night they had decided to rent a limo and go as a group to prom. He had harbored a crush on Felicity for years, but had never allowed himself to act on it. First, there had been Laurel. God, what a trainwreck that had been. Then McKenna. Then… well you got the point. He still didn’t think he deserved Felicity, but god did he want to know what she tasted like. Every inch of her. He would’ve settled for her lips. Which had been his intention with prom.

 

Then Tommy had picked him up and the drinking started. Within minutes the conversation had floated to Felicity and it was then that Oliver learned the simple truth: he was not alone in his desires. All it took was one look from Tommy to know what he was thinking. They had shared a girl once or twice before. They were comfortable with it, knew what they were doing. Hell, he and Tommy alone had kissed a few times during one or two of their rowdier nights out. They were comfortable together and Oliver knew his best friend like the back of his hand.

 

Initially, they hadn’t known how to approach it. This was Felicity - not some random blonde at a club that they could flash their Black Cards at in hopes of impressing her enough to invite them back to her bed. It had to be something she was comfortable with and really wanted. Honestly, they didn’t think they stood a chance.

 

Then her dress ripped, forcing them to retreat to an empty house filled with booze. Oliver wasn’t going to push anything, but a few drunk teenagers unsupervised typically only spelled out a couple of things. Especially when he and Tommy were involved.

 

Shuffling back over to the couch, Tequila in hand, he spread out three shot glasses on the center table. Lining them up, he tipped the liquor into the glasses and poured. Raising his own, he motioned for them to do the same.

 

“To best friends and new adventures.” He winked at Tommy before throwing his back. Felicity smiled, her lips stretching wide with happiness as she followed suit.

 

They had barely finished the first shot before Tommy had jumped up. Moving quickly towards the bar situated off the dining room, he muttered. “I can’t believe we just took tequila shots without limes or salt.”

 

Within seconds he was back, throwing the additional items onto the table. Oliver raised a brow in his direction. “What? If we’re going to take shots of tequila on prom night, we’re going to do it properly!” Typical Tommy. Always serious about the party he was engaged in.

 

They followed the process. Pour. Lick. Salt. Shot. Lime. Again.

 

It was on the third round, after Oliver’s hand had shot out to capture Felicity’s arm and pull it closer to lick the salt from her wrist, that she knew they were ready to take a break from the booze for a bit.

 

Pulling her arm away, she quickly broke eye contact with his dark gaze, trying to quell the burn moving down her body. Sure, part of it was the alcohol. But the other part was all Oliver. _God, she had to stop this._

 

Pulling herself together, Felicity said, “Tommy. Truth or dare?”

 

They locked eyes as he scrutinized her carefully before responding. “Dare.”

 

Frack. She had always been terrible at coming up with dares. Truths were easy to pull and she loved mysteries. What could she dare Tommy Merlyn to do that he hadn’t already done a thousand times over?

 

An idea came to her, and as she giggled before getting ready to speak, she realized the tequila had most certainly begun to do its’ job.

 

“Tommy Merlyn, I dare you tooooo… kiss Oliver.” Her eyes were sparkling with laughter, and Oliver knew she thought he wouldn’t do it.

 

Her laughter died the second Tommy spun around, arm reaching out to grab behind Oliver’s neck. Pulling him in closer, Tommy smiled lazily at Oliver before closing the distance with his lips.

 

Felicity’s mouth dropped open as she watched her two best friends in the world essentially _make out_ in front of her. She was also trying to use her shock to cover the surprisingly large amount of heat washing over her as she watched their lips slant and pull together.

 

After a few heated seconds, they pulled away, breathing heavier. They weren’t the only ones. “Oh…. oh my god! Oh wow. Is it hot in this room?” Felicity cut herself off, closing her eyes and inhaling deeply before re-opening them. Both Oliver and Tommy were grinning smugly back at her, clearly enjoying her decomposure. She opened her mouth to speak when Oliver interrupted.

 

“Truth or dare Felicity?” His eyes were still alight with amusement and he clearly wanted to catch her off guard before she could compose herself. Not ready to take any chances just yet, she replied, “Truth.”

 

Boy was that the wrong answer.

 

Oliver began to hum, putting his finger to his lips in a jokingly manner. His smile began to stretch across his face and Felicity only had a second to realize that she had just made a very grave mistake.

 

“Have you ever thought about being with Tommy or I?”

 

Felicity almost choked, her cheeks tinting pink almost immediately.  A soft, “Yes,” is all that leaves her and she’s biting her lip and looking over at them and fuck they are both so disgustingly attractive, it makes her angry.

 

“Nuh-uh Felicity. You have to specify which one of us.” Tommy is almost whining when Oliver cuts in, “Yeah - c’mon, Felicity. We did your dare without a pause. You owe us.” He had a point. But she wasn’t sure if she was ready to admit that she wanted both of them sometimes. Almost all of the time, really. This wasn’t normal, was it? To want to be with both of your best friends, as a group? No. She wasn’t going to hold back. This was what she set out to do - experience and make memories.

 

She blinked at them once. Twice. Then reaching over for the bottle of tequila, she poured a shot. Licked her wrist. Poured the salt. Her eyes never left their direction, sweeping over both of them with a heat that Oliver never would have expected to have directed at him from Felicity, but god did he love it.

 

Tilting her head back, she swallowed the sweet burn and then bit into the lime. Putting everything back on the table, she said, “Both of you.”

 

She watched both of them jerk in shock. Oliver’s eyes were blown wide, the desire and interest apparent on his face. Tommy wasn’t faring much better. His hand had immediately gone to the collar of his shirt, pulling it to the side for more breathing room.

 

Felicity was feeling bolder and bolder by the minute, although she suspected the Tequila may be playing a role in that. She finds strength in the desire plainly written across both of their features to make her next move.

 

“I dare _both_ of you to kiss me.” Her voice is breathy and she unconsciously licks her lips just thinking about touching not one of them, but the both of them.

 

Oliver’s eyes track her tongue sliding across her upper lip and he feels himself harden at the sight. _Fuck_. His eyes swing slowly over to his best friend, and he nods infinitesimally.

 

They both move at the same time. Oliver reaches her first, hand sliding up her neck to her face. Cupping her cheek, he leans in slowly, his eyes searing into her until they close at the last second, his lips taking hers. Their lips slide together slowly, Oliver taking his time memorizing her. She feels his other hand tightening on her waist, pulling her even closer.

 

Oliver’s tongue is licking at the seam of her lips, and she moans, opening her mouth to his in a short gasp. His tongue slides in immediately, and it’s at that moment she feels Tommy’s lips ghosting across the side of her neck. _God she had been so lost in Oliver she had almost forgotten he was there._ She wasn’t likely to forget again.

 

Goosebumps erupt over her skin as Tommy begins planting slow, wet kisses up and down the line of her throat. His tongue and teeth are skating across her skin and she can feel her arousal pooling below. Between the both of them, Felicity was on sensory overload.

 

Oliver’s mouth breaks away from hers, moving immediately to the unoccupied side of her neck. Her head falls back, her mouth wide open in exquisite agony.

 

“Felicity,” Oliver’s voice is rough but teasing as he alternates biting and sucking down her throat. Bringing his lips up to the shell of her ear, he tugs gently before whispering, “How would you like for Tommy to go down on you?”

 

Her hips jerk forward automatically and they have their answer. His voice, even rougher, “Does the thought of his tongue licking up and down your pussy make you wet, ‘licity?”

 

“Fuck, yes. _Please._ ” Her control had shattered the minute they had put their lips on her. She was all in on... whatever this was. And Oliver was clearly the dominant one in the group, easily taking charge and leading them into each other.

 

Oliver grins against her neck, planting one last soft kiss before pulling back. He pulls her shirt up, her arms lifting in help. Tommy is licking his lips at the sight, unbelievably hard in anticipation of tasting her - had dreamed about this for _years._

 

Tommy grabs her hips, pushing her back onto the edge of the round sectional. His hunger growing at the sight of her spread in front of him. She’s panting, her eyes dark, but a soft smile lights up her face as she smiles down at him. He tugs at the waistband of the soft lounge pants adorning her waist, pulling them down her long legs and throwing them carelessly to the side.

 

Oliver is busying himself with the removal of her bra, flicking the front snap with practiced ease. As soon as the garment is off, his lips close around a nipple, flicking and tugging, all lips and teeth. Her hands tighten around his head, pulling him closer to her chest in encouragement.

 

Tommy begins at her ankles, placing a soft kiss to one before glancing up at her heavily. “I hope you’re ready Felicity.”

 

He smiles at her resulting groan and begins moving his lips up her leg, stopping at her knee to place a kiss and then continuing up. His hands are trailing the path of his lips, gently caressing as he makes his way up to her pussy.

 

He cups her sex, rubbing her gently while watching her face - gauging her reaction. Her hips are moving restlessly on the couch, the combination of Tommy and Oliver’s tongues and hands and _god she never knew it could be this good._

 

Tommy’s pulling her thong down and off, throwing it off to the side to be lost in the growing pile of their clothes. He pulls off his own shirt for good measure, smirking at her look of appreciation as she takes in his chest. He isn’t nearly as toned as Oliver, but he’s lean and lithe and he knows the ladies appreciate it.

 

Before she can blink, he has a finger running up and down her slit, teasing her. She’s about to ask for more, when his tongue slips in between her folds, imitating his finger’s previous movements.

 

Felicity’s moan is muffled by Oliver’s mouth claiming hers once again. She allows him to take the lead, _as always_ , his hands moving to pin hers above her head as he ravages her lips, mimicking Tommy’s movements below.

 

_Fuck._ How did they learn how to kiss in tandem? Nevermind, she didn’t want to know.

 

Tommy’s pulling her thighs open wider, bringing her closer to him as his tongue laps up her juice, suckling at her clit. Her hips are moving and his hands tighten around her thighs in warning. He licks his lips, his dark eyes piercing her. “You need to behave for me, ‘licity. Can you do that?”

 

“Fu- yes- yes, I’ll behave, just please don’t stop.” She’s so close, and Oliver is back at her neck again, suckling hard and she just knows she will have marks in the morning. It’s hard to care about that when she has two devastatingly handsome boys bringing her to the edge.

 

Tommy seems appeased with her admission, continuing to drink her in. She’s trying her best, but he can sense she’s close and he pushes forward at a punishing pace. His tongue is sliding back and forth, side to side as her moans increase. Oliver catches his eye, a slight imperceptible nod. Then they’re both biting down, Oliver on the sensitive spot on her neck (one which he has become very fond of), and Tommy on her clit.

 

She shatters with a long moan, muttering “Oh my god, oh my _god_ ,” over and over as she comes down. Tommy’s lapping at her with all he’s worth, not letting a drop go to waste. She tasted fucking exquisite, just like he always knew she would.

 

Both men pull away, leaving her in a boneless heap on the couch. Her eyes are closed, completely relaxed as she recovers. Wow.

 

Tommy’s thumb moves to swipe at his mouth, before Oliver’s hand stops him short. He pulls Tommy’s thumb into his mouth, sucking the taste of Felicity off of his thumb before surging forward to claim the rest of her off of his lips.

 

Felicity watches them from her place on the couch, her eyes are hazy as she drinks them in. She doesn’t know why she finds watching them together so arousing, but she can already feel the twinges of arousal eating at her again.

 

Oliver moans, pulling away from Tommy, his own tongue swiping over his lips as if trying to memorize the taste of her. He squeezes Tommy’s neck, resting his forehead against his for a second before turning back towards their girl.

 

“I’m going to fuck you now, Felicity. And while I do, I want to watch you taking Tommy’s cock into your pretty little mouth.” His tone was clear and left no room for arguments. He heard Tommy mutter a “Fuck, yeah” behind him,

 

Felicity knew that they were experienced, far more experienced than her for sure. But hearing Oliver talk like this was awakening something inside of her. She was out of her mind for him, for them.

 

She pushs herself onto her knees, curling her finger at Tommy and motioning him to come towards her. His resident smirk had found place on his face again as he quickly unbuttoned his black slacks, stripping both his pants and boxers down and off in record speed. He had barely taken a step towards her before her small hand wrapped around his length.

 

He growled low in his throat, the pressure of her hand feeling remarkable on his aching dick. Felicity stroked him slowly, up and down, delighting in the feel of him hardening more in her grasp.

 

She felt Oliver’s presence behind her, leaning over to messily kiss his way down her spine. He must have shed his clothes at some point because she could feel his equally hard cock pressing into her. And lord help her, he was _big_. Like, _oh god- oh god, will he even fit,_ big.

 

His hand felt rough against her skin as pushed down on her back, and she licked at the slit of  Tommy’s cock just as she felt Oliver lining up with her pussy. The head of his length was teasingly running up and down her slit, pushing in a little and pulling back out, just as she was licking up and down Tommy’s head, hovering her mouth over it and pulling back.

 

They were mimicking each other, she realized. Now she understood how they had done it to her previously. They had a synchronicity, a balance and understanding of each other. It was amplifying every feeling and every touch.

 

She was ripped from her thoughts as Oliver surged forward, sliding into her slick arousal in one thrust. She groaned, her voice vibrating around Tommy’s dick and pulling a low moan from him as well.

 

She could feel Oliver’s fingers gripping her waist almost to the point of pain as he steadied himself within her. Her tongue was swirling around Tommy’s head, moving the precum around his head before taking him fully into her mouth. His hips bucked into her in surprise, a low “Fuck” slipping from his lips, head thrown back in bliss.

 

Behind her, Oliver was setting a punishing pace as his control wavered. His hands on her waist were pulling her back into him repeatedly, his cock reaching far into her and hitting a spot she had only dreamed of.

 

She didn’t think it was possible, but she felt herself growing more aroused at the sounds he was making. They alternated between grunts and soft, whining noises as his hips pistoned into hers. It spoke of his uncontrollable fervor, and it thrilled her to bring _Oliver_ \- strong, unwavering, _Oliver_ , to his knees.

 

With every sharp thrust she took Tommy into her mouth further, the three of them a mess of moans, grunts and sharp breaths.

 

Tommy’s voice echoed through the living room, “Oliver - fuck, Oliver are you close? Please say yes.” His hips had begun thrusting into Felicity’s mouth, his hand already entangled in her hair as he fought to keep his sanity. He looked up at Oliver for affirmation and his hips buckled.

 

Oliver’s arms were straining with restraint, his hair was slick as sweat dripped down the sides of his face. His eyes were fluttering between open and shut and he was biting his lip while he continued to fuck her.

 

“Ye- yes, fuck yes. God, buddy, she is so tight - it’s heaven.” He slipped one hand off her waist, reaching down to rub at her clit while he continued to push in and out of her. Felicity shuddered, knowing they were reaching the end. Taking a page from Oliver’s direction, she moved her hand down to cup Tommy’s balls, massaging them slightly to the same rhythm as Oliver’s finger.

 

A few seconds later, she felt Tommy’s balls tighten and then he was releasing quickly into her mouth. She moaned, taking in every drop of him as he continued to pulse inside of her mouth. Her pussy tightened at the taste and Oliver groaned at the feeling of her walls clenching around him. He had never been so hard in his life, nothing - no one - had ever felt this good before.

 

His finger sped up and he pinched down on her clit, bringing Felicity to her second orgasm of the night. As soon as her walls began to pulse around his cock, he was gone with them. With one last thrust and groan, he began to shoot into her, his hips continuing to buck into her slowly as he released himself.

 

The three bodies continued to slowly rock into one another as they came down. After a beat, she felt Oliver take a deep breath and slowly ease out of her. She winced a little, knowing she was going to be sore as hell tomorrow. “Fuck, that was amazing,” Oliver groaned as he flopped back onto the couch.

 

Felicity could only nod her head in approval, the past hour’s events taking their toll on her exhausted body. She felt Oliver lean over to press a soft kiss on her shoulder before wrapping an arm around her midsection. Tommy followed shortly after, running a hand slowly up and down her midsection before his leg wrapped in between hers. Felicity grinned softly to herself, _they were really going out with a bang_.

 

Snorting quietly to herself and telling her mind to shut it, she closed her eyes and they drifted quickly into a slumber, wrapped around each other on the plush cushions.

  
Felicity and Oliver would leave for Boston in three short months, but this would not be the last time they had allowed themselves to enjoy one another’s company beyond friendship.


End file.
